US20110293549A1

US20110293549A1 - Composition, method and kit for enhancing hair

Info

Publication number: US20110293549A1
Application number: US12/698,823
Authority: US
Inventors: Michael C. Brinkenhoff
Original assignee: Athena Cosmetics Inc
Current assignee: PHARMA PATENT HOLDING Inc
Priority date: 2009-02-03
Filing date: 2010-02-02
Publication date: 2011-12-01
Also published as: US20150190322A1; US9006291B2; US20130046024A1

Abstract

Compositions for application and methods of application of a composition to modify hair. In one embodiment, a composition includes a compound (molecule) represented by:

- wherein A and B are individually selected from a hydrogen, a hydroxyl group and a halogen, with the proviso that when one of A and B is a hydroxyl group, the other of A and B is a hydrogen and when one of A and B is a halogen, the other of A and B is a halogen or a hydrogen;
- wherein Z is, for example, an aryl moiety; and
- wherein X₁and X₂are, for example, individually selected from a hydrogen and an alkyl moiety,
- wherein R₁and R₂are individually selected from an oxo, a hydroxyl or an ester group;
- wherein y is 0 or 1, x is 0 or 1 and x and y are not both 1, or a salt.

Description

CROSS-REFERENCE TO RELATED APPLICATION

The application claims the benefit of the earlier filing date of co-pending U.S. Provisional Patent Application No. 61/149,661, filed Feb. 3, 2009 and incorporated herein by reference.

FIELD

Composition, method and kit for enhancing human hair including eyelashes.

BACKGROUND

Certain therapeutic agents have been known to induce hair growth. One example is Minoxidil, 6-(1-piperidinyl)-2,4-pyrimidane-diamine-3-oxide (U.S. Pat. Nos. 3,382,247 and 3,644,363). Minoxidil was originally prepared and sold for use as an antihypertensive. It was observed that, associated with the use of Minoxidil for this latter purpose, Minoxidil use also produced an increase in hair growth and thickness as reported in U.S. Pat. Nos. 4,139,619 and 4,968,812. Today, Minoxidil is marketed under the trademark Rogaine® by Pfizer for the treatment of baldness on the scalp for men (alopecia androgenetica) and women. Another example is finasteride (Propecia®), marketed by Merck & Co. Finasteride was originally developed for benign prostatic hypertrophy, and was found to be effective in the treatment of alopecia androgenetica as reported in U.S. Pat. No. 4,968,812.
Among the drugs introduced for lowering intraocular pressure are molecules of the family prostaglandin F2. The Upjohn Company identified a prostaglandin F2α analog, commonly known as Latanoprost and whose chemical name is isopropyl-(Z)-7[(1R,2R,3R,5S)3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenyl p-entyl]cyclopentyl]-5-heptenoate. Latanoprost is marketed by Pharmacia & Upjohn (currently a part of Pfizer) under the trademark Xalatan® for the reduction of elevated intraocular pressure in patients with glaucoma and ocular hypertension. The form is a Latanoprost optical solution of 0.005% (50 μg/ml), and is applied by dropper directly onto the eye. One drop generally contains approximately 1.5 μg of Latanoprost.
In the course of its use for reduction of intraocular pressure, Latanoprost has been reported to cause, in some patients, an increasing pigmentation and growth of eyelashes. U.S. Pat. No. 6,262,105 stated that the use of Latanoprost leads to increased length of lashes, increased numbers of lashes along the normal lash line, increased thickness and luster of lashes, increased auxiliary lash-like terminal hair in transitional areas adjacent to areas of normal lash growth, increased lash-like terminal hairs at the medial and lateral canthal area, increased pigmentation of the lashes, increased numbers, increased length, as well as increased luster, and thickness of fine hair on the skin of the adjacent lid, and increased perpendicular angulation of lashes and lash-like terminal hairs.
Alcon, Inc. (“Alcon”) introduced a prostaglandin F2α analog, commonly known as Travoprost whose chemical name is isopropyl (z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[(α,α,α-trifluoro-m-tolyl)oxyl]-1-butenyl]cyclopentyl]-5-heptenoate as a glaucoma treatment. Alcon also sought patent protection for Travoprost for growing hair in U.S. Patent Application No. 2003/0199590.
Allergan, Inc. (“Allergan”) introduced Bimatoprost whose chemical name is cyclopentane N-ethyl haptanamide-5-cis-2-(3α-hydrosy-5-phenyl-1-trans-pentenyl)-3,5-dihydroxy,[1α, 2α, 3α, 5α) for treating glaucoma. U.S. Pat. No. 7,351,404 is directed at the use of this molecule and similar molecules for growing hair, including eyelashes. Allergan distinguishes the Bimatoprost molecule from other prostaglandins on the basis that Bimatoprost is a prostamide.
U.S. Pat. Nos. 5,886,035 and 5,985,920 describe fluorine containing prostaglandin derivatives for use as a preventive or therapeutic medicine for an eye disease such as glaucoma or elevated intraocular pressure.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows a process flow from a Corey acetate derivative to a difluoro compound that includes an ethyl amide.

DETAILED DESCRIPTION

Compositions for topical application, methods of topical application of a composition to enhance hair, and a kit are described. Enhancing hair as used herein includes stimulating or promoting growth of existing hair, including stimulating or promoting a bulb or cells in a follicle associated with the formation of an actual hair into hair growth. Hair growth in this sense includes an increase in length and/or an increase in diameter of a hair. Enhancing hair also includes conditioning hair and/or cosmetically improving the appearance or beauty of the hair such that hair subject to the compound or a composition including the compound appears or feels longer, thicker and fuller. Enhancing hair also includes darkening the hair. The location of the hair includes the scalp (e.g., scalp hair), eyelid (e.g., eyelashes), and brow (e.g., eyebrows) and any other portion of human skin where hair exists or may be desired.
In one embodiment, a composition includes an effective hair enhancing amount of a compound represented by the following formula:
wherein the dashed bonds represent a single or double bond that can be in the cis or trans configuration; R and R′ are individually selected from hydrogen, or a C₁-C₆straight or branched chain alkyl (e.g., methyl, ethyl, isopropyl); X is a halide (e.g., F, Cl, Br, I) a halide-containing group (e.g., CF₃), or hydrogen; either y=0 and x=1 or y=1 and x=0. The molecule may be characterized as a difluoro prostaglandin or prostaglandin-like compound because its backbone resembles a prostaglandin.
A difluoro compound may be in a molecular free form (a molecule) or an acceptable salt thereof (a compound). An acceptable salt is a dermatologically acceptable salt or a pharmaceutically acceptable salt. An example of a salt is a hydrohalide salt of the molecule such as a hydrochloride salt. In one embodiment, the resulting salt compound will have the proton from the hydrohalide bonded to the nitrogen of the molecule and be charge balanced by the halide. Throughout this description, unless specifically indicated a reference to a compound includes a molecule or a compound.
In another embodiment, the compound has the following formula:
wherein R, R′, X, y and x are defined above, or an acceptable salt thereof.
In a particular embodiment, the compound is one of the following molecules or a salt thereof:
In one embodiment, one or more compounds described above is/are mixed with a dermatologically compatible vehicle or carrier to form a composition. Suitable vehicles include, for example, aqueous solutions such as e.g., physiological salines, oil (e.g., castor oil), solutions, foams, creams or ointments. Suitable vehicles furthermore may contain dermatologically compatible preservatives such as e.g., benzalkonium chloride, surfactants like e.g., polysorbate 80, liposomes or polymers, for example, methyl cellulose, polyvinyl alcohol, polyvinyl pyrrolidone and hyaluronic acid; these may be used for increasing the viscosity.
In one embodiment, dermatological compositions for topical treatment for enhancing hair that include an effective hair enhancing amount of one or more compounds as defined above and a dermatologically compatible carrier are also disclosed. Effective amounts of the active compounds may be determined by one of ordinary skill in the art but will vary depending on the compound employed, frequency of application and desired result. An amount of a compound or compounds will generally range from about 0.0000001 to about 10 percent, by weight, of the dermatological composition, preferably from about 0.0001 to about 10 percent, by weight, of total dermatological composition.
In another embodiment, a composition may include a combination of difluoro prostaglandin or prostaglandin-like compounds described or a compound(s) and other hair treatment aids such as an antioxidant (e.g., Vitamin E), a vasodilator (e.g., minoxidil), an antimicrobial (e.g., benzoyl peroxide), or an anti-inflammatory (e.g., hydrocortisone, cyclooxygenase inhibitor, lipooxigenase inhibitor).
The composition may be topically applied to the dermis of, for example, a human in an area desired for enhancing hair such as direct application to existing hair or the dermis in an area desired for hair enhancing as opposed to an indirect application such as to the surface of the eye. Such location may include the scalp, eyelash area or eyelid or brow of a male or female. Application of the compound(s) or composition to a base of a hair or hairs may create a wicking action where the compound(s) are drawn up the length of the hair or hairs. Repeated application for a sustained period of time (e.g., daily for several weeks or more (e.g., one month to several months)) may be desired.
Where hair is not present, the composition may be applied directly to the dermis where hair growth is desired. This may include the scalp where, for example, a density of existing hair has been reduced due to alopecia or other mechanism (e.g., hair loss as a side effect to chemotherapy treatment). In certain Asian cultures, an absence of pubic hair is considered bad luck and can be a serious problem, particularly in women. The composition may be applied to the pubic area to address this problem. In one embodiment, repeated daily topical application of a composition to an area of the dermis where hair growth is desired may continue until hair growth is effected and may continue periodically (daily, weekly) to maintain such growth. In one embodiment, such topical application to the dermis may, for example, utilize a delivery vehicle including the composition that is a foam or cream.
To enhance eyelashes, a composition including at least one difluoro prostaglandin or prostaglandin-like compound as described above may be applied at the base of an eyelid adjacent to or where hair grows from the follicles (e.g., along the lash line). Alternatively or additionally, the composition may be applied to the eyelashes themselves. Repeated application for consecutive days, weeks or months (e.g., regular daily application for six months) of the composition to eyelashes or areas of eyelid dermis associated with eyelashes (e.g., the base of an eyelid containing follicles in which eyelashes grow) will condition and cosmetically enhance existing eyelashes such that the eyelashes appear longer, thicker and fuller. Such application will also stimulate or promote the growth of eyelashes.
In another embodiment, a kit is disclosed. The kit may include the composition of at least one difluoro prostaglandin or prostaglandin-like compound as described above in a dermatologically compatible vehicle or carrier in a container. The container includes an amount of the composition for repeated application over a period, such as enough of the composition for daily application over a period of six months. The container may also include an applicator, such as a mascara brush or other instrument for application of the composition to skin. In the case of a composition in the form of a foam, the container may be pressurized and include a nozzle to dispense a desired amount onto the hand of a user.

Example 1

Synthesis of 3,3-difluoro-4-phenoxybut-1-enyl-3,5-dihydroxycyclopentyl-hept-5-enoic acid

Starting from a Corey acetate derivative, an omega chain backbone, such as dimethyl 2-oxo-3-phenoxy-propyl phosphonate is added via an exchange reaction. The oxo group in the 2 position is preserved in the formed intermediate and then reduced with a fluorine compound to produce a difluoro precursor. Subsequently, the alpha chain is added at another site of the Corey acetate derivative yielding 3,3-difluoro-4-phenoxybut-1-enyl-3,5-dihydroxycyclopentyl-hept-5-enoic acid.

Example 2

Synthesis of 3,3-difluoro-4-phenoxybut-1-enyl-3,5-dihydroxycyclopentyl-menthylhept-5-enoate

To the 3,3-difluoro-4-phenoxybut-1-enyl-3,5-dihydroxycyclopentyl-hept-5-enoic acid is added iodomethane in a solution of tetrahydroturan (THF) to form 3,3-difluoro-4-phenoxybut-1-enyl-3,5-dihydroxycyclopentyl-methylhept-5-enoate.

Example 3

Synthesis of 3,3-difluoro-4-phenoxybut-1-enyl-3,5-dihydroxycyclopentyl-N-ethylhept-5-enamide

To the 3,3-difluoro-4-phenoxybut-1-enyl-3,5-dihydroxycyclopentyl-methylhept-5-enoate is added ethylamine in water to form 3,3-difluoro-4-phenoxybut-1-enyl-3,5-dihydroxycyclopentyl-N-ethylhept-5-enamide.
FIG. 1 shows a process flow from a Corey acetate derivative to the acid, to the ester and then to an ethyl amide (Compound 3). U.S. Pat. No. 5,886,035 also describes a method of preparing difluoro-prostaglandin derivatives but does not describe the use of such derivatives in hair (eyelash) growth.
The following examples provide representative compositions including a difluoro compound such as Compound 3:

Example 4

Eyelash Composition


	Ingredient	Percentage

1.	Water (Aqua)	97.791
2.	Sodium Chloride	0.877
3.	Panthenol	0.020
4.	Citric Acid	0.030
5.	Phenoxyethanol	0.300
6.	Chlorphenesin	0.300
7.	Disodium Phosphate	0.142
8.	Difluoro Compound	0.024
9.	Alcohol	0.216
10.	Cellulose Gum	0.300

Example 5

Eyelash Composition


	Ingredient	Percentage

1.	USP Water	94.519
2.	Sodium Chloride	0.077
3.	Phosphoric Acid	0.03
4.	Phenoxyethanol	0.3
5.	Chlorphenesin	0.3
6.	Disodium Phosphate	0.142
7.	Cellulose Gum	0.36
8.	Biotin	0.5
9.	Glycerin	0.6
10.	Swertia Japonica Extract	0.045
11.	Saw Palmetto Extract	0.064
12.	Camellia Sinensis (White Tea) Leaf	0.054
	Extract
13.	Panax Ginseng	0.075
14.	Octapeptide-2	0.93
15.	Biotinoyl Tripeptide-1	0.93
16.	Wheat Protein	0.25
17.	Calendula	0.8
18.	Difluoro Compound	0.024

Example 6

Eyelash Composition


	Ingredient	Percentage

1.	USP Water	96.031
2.	Actiphyte of Rosemary	0.025
3.	Phosphoric Acid	0.001
4.	Phenoxyethanol	0.3
5.	Chlorphenesin	0.3
6.	Disodium Phosphate	0.985
7.	Cellulose Gum	0.36
8.	Biotin	0.24
9.	Panthenol	0.25
10.	Actiphyte of Nettles	0.1
11.	Actiphyte of Horsetail	0.098
12.	Actiphyte of Psoralea Seed	0.15
13.	Mulberry Root Extract	0.07
14.	Actiphyte of Japanese Green Tea	0.25
15.	Glycerin	0.6
16.	Difluoro Compound (in 10%	0.24
	Ethanol Solution)

Example 7

Scalp Composition


	Ingredient	Percentage

1.	Water	95.00000
2.	Acrylates Copolymer	1.50000
3.	Glycerin	1.00000
4.	Phenoxyethanol	0.80000
5.	Sodium Cocoyl Glutamate	0.35000
6.	Chlorphenesin	0.30000
7.	Polysorbate	0.25000
8.	Trifluoromethyl Dechloro	0.24000
	Ethylprostenolamide
9.	Disodium EDTA	0.10000
10.	Fragrance	0.09610
11.	Aminomethyl Propanol	0.09000
12.	Panax Ginseng Root Extract	0.08000
13.	Panthenol	0.08000
14.	Ginko Bilola Leaf Extract	0.05000
15.	Biotin	0.05000
16.	Serenoa Serrulata Fruit Extract	0.00640
17.	Swertia Japonica Extract	0.00450
18.	Hydrolyzed Wheat Protein	0.00300

In another embodiment, compositions for topical application and methods of topical application of a composition to modify hair are described wherein the modification includes increased curl of hair on a subject or hair that is not biologically attached to or is not naturally a part of a subject (e.g., hair of a wig or extension) (“non-natural hair”). In another embodiment, the modification includes increased curl of the hair together with conditioning hair and/or cosmetically improving the appearance or beauty of the hair (e.g., increased look and feel of softness and silkiness). Thus, the compositions described may be applied to existing hair on the scalp or eyelashes or non-natural hair to increase the curl and/or the look and feel of the hair. In one embodiment, a composition includes an effective amount of a compound represented by the following formula:
wherein the dashed bonds represent a single or double bond and when a bond in either chain is a double bond, cis or trans configuration is contemplated;
wherein A and B are individually selected from a hydrogen atom, a hydroxyl group (—OH) and a halogen atom (e.g., a fluorine atom), with the proviso that when one of A and B is a hydroxyl group, the other of A and B is a hydrogen atom and when one of A and B is a halogen atom, the other of A and B is a halogen atom or a hydrogen atom;
wherein Z is a cycloalkyl moiety having from three to seven carbon atoms, an aryl moiety including from four to ten carbon atoms or a heteroaryl moiety including three to nine carbon atoms and at least one heteroatom selected from nitrogen, oxygen and sulfur; and
wherein X₁and X₂are individually selected from a hydrogen atom, an alkyl moiety having from one to six carbon atoms,
and
R⁵is an alkyl moiety having from one to six carbon atoms;
wherein R₁and R₂are individually selected from an oxo group (═O), a hydroxyl group (—OH) or an ester group (—O(CO)R₆), and R₆is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms, and —(CH₂)_mR₇wherein m is 0 or an integer of from 1 to 10, and R₇is cycloalkyl group, having from three to seven carbon atoms, or an aryl or heteroaryl group, as defined above;
wherein y is 0 or 1, x is 0 or 1 and x and y are not both 1.
The compound may be in free form (a molecule) or an acceptable salt thereof (a compound) such as a cationic or anionic salt formed at the nitrogen atom of the molecule, in association with a carrier adapted for topical application to mammalian skin. Unless specified, reference to a compound will include a molecule or a compound.
In one embodiment, the compound is represented by the following formula:
wherein Y is selected from an alkyl group, a halogen atom (e.g., fluorine, chlorine), a nitro group, an amino group, a thiol group, a hydroxy group, an alkyloxy group, an alkylcarboxy group, a halo substituted alkyl wherein the alkyl includes from one to six carbon atoms, and n is 0 or an integer of from 1 to 3, or an acceptable salt thereof.
In another embodiment, the compound has the following formula:
wherein A, B, X₁, X₂, Y and n are as defined above, or an acceptable salt thereof.
In a particular embodiment, the compound is selected from any of compounds (1)-(5) above or a molecule having one of the following formulas or a salt thereof:
Compounds (6)-(9) may be prepared using techniques known in the art including, for example, techniques described in U.S. Pat. Nos. 5,001,153; 5,422,368; 5,510,383; and 5,607,978.
In one embodiment, the one or more compounds described above (including compounds (1)-(9) is/are mixed with a dermatologically compatible vehicle or carrier. Suitable vehicles include, for example, aqueous solutions such as e.g., physiological salines, oil (e.g., castor oil), water solutions, water/alcohol solutions or ointments. Suitable vehicles furthermore may contain dermatologically compatible preservatives such as e.g., benzalkonium chloride, surfactants like e.g., polysorbate 80, liposomes or polymers, for example, methyl cellulose, polyvinyl alcohol, polyvinyl pyrrolidone and hyaluronic acid; these may be used for increasing the viscosity.
In one embodiment, dermatological compositions for topical treatment for inducing or stimulating modification of existing hair including increased curl which include an effective hair modifying amount of one or more compounds as defined above and a dermatologically compatible carrier are also disclosed wherein the modification includes increased curl of hair or increased curl. Effective amounts of the compound may be determined by one of ordinary skill in the art but will vary depending on the compound employed, frequency of application and desired result, and the compound will generally range from about 0.0000001 to about 50%, by weight, of the dermatological composition, preferably from about 0.001 to about 50%, by weight, of total dermatological composition, more preferably from about 0.1 to about 30%, by weight of the composition. In another embodiment, a composition may include a combination of compounds described or a compound(s) and other hair treatment aids such as an antioxidant (e.g., Vitamin E), a vasodilator (e.g., minoxidil), an antimicrobial (e.g., benzoyl peroxide), or an anti-inflammatory (e.g., hydrocortisone, cyclooxygenase inhibitor, lipooxigenase inhibitor).
The composition may be topically applied to existing hair and retained on the hair. Such location may include the scalp or eyelash area of a male or female. Repeated application for a sustained period of time (e.g., daily for several weeks or more (e.g., one month to several months)) may be desired. The composition may be beneficial to persons that naturally have straight scalp hair to aid in the curl of such hair. Evidence of the effectiveness of a composition of compound (3) (dechloro-dihydroxy-difluoro-ethylcloprostenate) and, alternatively, of compound (8) (trifluoromethyl dechloroethyl prostenolamide) in application to generally straight Asian hair indicates a profound curling effect.
In one embodiment, the composition is suitable for modifying eyelashes. To modify eyelashes, a composition would be provided to a subject with instructions on use (e.g., by instructions on or with a kit, the kit including the composition and the instructions). The subject would be instructed to apply the composition to eyelash hair. In addition to modifying the eyelashes (e.g., increasing the curl and/or look and feel), it is anticipated that application to a hair follicle will increase the thickness (e.g., diameter) of the follicle.
In one embodiment, the composition may be topically applied to hair on the scalp. For example, a subject interested in establishing a curl to a portion of the subject's scalp hair or improving a natural curl, would be instructed (e.g., by instructions on or with a kit) to topically apply the composition to the desired portion of the hair and to leave the composition on the hair. To improve or sustain the curl over a period of time (e.g., days, weeks), the subject would be instructed to repeat the application for a period ranging from days to weeks.
In another embodiment, the applications described above may be used to modify non-natural hair (e.g., hair not biologically attached to or is not naturally a part of a subject). Examples of such hair include, but are not limited to, wigs and hair extensions.
In another embodiment, a kit is disclosed. The kit may include the composition of at least one compound having the formula III or IV as described above in a dermatologically compatible vehicle or carrier in a container. The container includes an amount of the composition for repeated application over a period, such as enough of the composition for daily application over a period of six months. The container may also include an applicator, such as a mascara brush or other instrument for application of the composition to skin. In the case of a composition in the form of a foam, the container may be pressurized and include a nozzle to dispense a desired amount onto the hand of a user.

Example

The following example used trifluoromethyl dechloroethyl prostenolamide (TDP) as a compound. TDP has the following formula:
A solution of TDP was prepared including 97.6 percent water, 0.24 percent TDP and 2.16 percent ethyl alcohol. Samples of human hair separated from a subject were treated with water alone while others were treated with the TDP solution. The treatment involved dipping the dry hair samples into the water and TDP solutions to one minute. Unexpectedly, there appeared a definite increase in curl in each of the hair samples when treated with the TDP solution. The hair treated with water alone did not show similar curl. The results are illustrated in FIG. 1. In addition, the hair treated with the TDP solution had a noticeable and palpable increase in the look and feel of softness and silkiness compared to the hair treated with the water alone.
In the preceding detailed description, reference is made to specific embodiments thereof. It will, however, be evident that various modifications and changes may be made thereto without departing from the broader spirit and scope of the following claims. The specification and drawings are, accordingly, to be regarded in an illustrative rather than a restrictive sense.

Claims

1. A composition comprising a compound of the formula:

wherein the dashed bonds represent a single or double bond; R and R′ are individually selected from the group consisting of hydrogen, a C₁-C₆straight or branched chain alkyl; X is selected from the group consisting of a halide, a halide containing group or a hydrogen; y is 0 or 1, x is 0 or 1 and x and y are not both 1 or not both 0; or a salt thereof.

2. A composition of claim 1, wherein the compound has the formula:

3. A composition of claim 2, wherein the compound has the formula:

4. A composition of claim 2, wherein the compound has the formula:

5. A composition of claim 2, wherein the compound has the formula:

6. A composition of claim 2, wherein the compound has the formula:

7. The composition of claim 1, further comprising a dermatologically acceptable carrier.

8. A method comprising:

directly applying to dermis or hair on the dermis an amount of a composition comprising a compound of the formula:

wherein the dashed bonds represent a single or double bond, R and R′ are individually selected from the group consisting of hydrogen, a C₁-C₆straight or branched chain alkyl, X is selected from the group consisting of a halide, a halide containing group or a hydrogen, y is 0 or 1, x is 0 or 1 and x and y are not both 1, or a salt thereof.

9. The method of claim 7, wherein the dermis includes an eyelid.

10. The method of claim 8, wherein the compound has the formula:

11. The method of claim 8, wherein the compound has the formula:

12. The method of claim 8, wherein the compound has the formula:

13. The method of claim 8, wherein the compound has the formula:

14. The method of claim 8, wherein the composition further comprises a dermatologically acceptable carrier.

15. A kit comprising:

a container;

a composition comprising a compound of the formula:

wherein the dashed bonds represent a single or double bond; R and R′ are individually selected from the group consisting of hydrogen, a C₁-C₆straight or branched chain alkyl; X is selected from the group consisting of a halide, a halide containing group or a hydrogen; y is 0 or 1, x is 0 or 1 and x and y are not both 1 or not both 0; or a pharmaceutically acceptable salt thereof, and

wherein the container includes an amount of the composition for repeated application over a period.

16. The kit of claim 15 further comprising an applicator.

17. The kit of claim 15, wherein the compound is selected from at least one of the following:

18. A method comprising:

directly applying to hair an effective amount of a composition to effect a curl of the hair, the composition comprising a compound of the formula:

wherein the dashed bonds represent a single or double bond;

wherein A and B are individually selected from a hydrogen atom, a hydroxyl group (—OH) and a halogen atom (e.g., a fluorine atom), with the proviso that when one of A and B is a hydroxyl group, the other of A and B is a hydrogen atom and when one of A and B is a halogen atom, the other of A and B is a halogen atom or a hydrogen atom;

wherein Z is a cycloalkyl moiety having from three to seven carbon atoms, an aryl moiety including from four to ten carbon atoms or a heteroaryl moiety including three to nine carbon atoms and at least one heteroatom selected from nitrogen, oxygen and sulfur; and

wherein X₁and X₂are individually selected from a hydrogen atom, an alkyl moiety having from one to six carbon atoms,

and

R⁵is an alkyl moiety having from one to six carbon atoms;

wherein R₁and R₂are individually selected from an oxo group, a hydroxyl group or an ester group, and R₆is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms, and —(CH₂)_mR₇wherein m is 0 or an integer of from 1 to 10, and R₇is cycloalkyl group, having from three to seven carbon atoms, or an aryl or heteroaryl group, as defined above; and

wherein y is 0 or 1, x is 0 or 1 and x and y are not both 1, or a salt thereof.

19. The method of claim 18, wherein the hair comprises eyelashes.